This is an interesting discussion, but I think people are putting too much emphasis on coaches who are a long, long (long) way from getting the most wins. Yes, Capel's in a good position right now, but you're making a prediction for something 20-30 years down the road. This is like predicting Prince Fielder will pass Bonds in career HR's - possible, but there's too much time and too many variables for that to be the least bit likely. Self is a little better, but he's still Albert Pujols.
If you ask me, the most likely to beat K is Calhoun, followed by Boeheim. What they have to do is pretty simple - hang on for about 2 years (or maybe just 1 for Calhoun
) after K retires. That said, I think the most likely outcome is that K holds onto the #1 spot for quite a while.